
Vacation rentals with a pool in Province of Grosseto
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Top-rated rentals with a pool in Province of Grosseto
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Popular amenities for Province of Grosseto rentals with a pool
House rentals with a pool

S.Ilaria - Private pool Villa with 2 bedrooms
Fabulous setting in the middle of fabulous Tuscany. The views from the house were stunning! The farmhouse itself was so charming - every detail. We enjoyed dinners on the covered patio, evening walks on the gravel road through the countryside and lounging by the pool with a glass of red wine. The setting is also the perfect location for day trips to nearby cities. We visited Montalcino, Montepulciano, Siena, Pienza and Cortona. Highly recommend!

Stunning new house with amazing sea view and pool
One of the best views you will find! Place is clean and comfortable. AC in every room and worked well. Probably the best washer dryer we had in Italy :) Incredibly responsive host. Highly recommend!

Il Camino: cosy & artfully inspired country house
Thomas was so sweet and helpful. He was an absolute gentleman and wonderful host. The views were amazing. Very homey and decorated in the Tuscany style. Close to town but perfect for a quiet escape in the Tuscan countryside.

3 rooms in the woods, with swimming pool - Fonte di Sotto
Margherita is very welcoming, good tips for the must-sees of the region, we had a very pleasant stay, comfortable bedding, spacious and well arranged house, a splendid swimming pool with views (about 20m long), lots of sunbed, air conditioning everywhere. So yes, the dirt road to get there may seem long sometimes but that's the price of tranquility. Only downside, the risk of having noisy neighbors on the lower or upper floor (which we had for 3 days).

Country chic house in a village,private pool,wiFi
Lorenzo met us on the street to walk us to the villa and showed us everything with a very warm welcome! The views are breathtaking! We found the location to be an excellent base to visit all of the surrounding towns. Having Grazia Franchini (see the host’s guidebook) prepare and serve dinner for us in the villa after a fabulous day of Brunello wine tastings was such a treat! Would definitely return to the area and stay here again but next time will set aside a day just to relax by the pool!

Tolomei Farmhouse in Stone
Everything is great, great place to stay with a small wellness area. We felt very comfortable!

Country House in the Crete Senesi
We feel so lucky to of found Guido and his beautiful house. Firstly Guido could not be more helpful, so responsive, friendly and has the best recommendations! He made sure the house was spotless for our arrival, even the pool is so clean it was perfect. The house itself is stunning, stays lovely and cool in the heat but the garden is just drenched in sunshine. Guido has made sure you can bask in the sunshine by the pool or chill out in shade in the height of the afternoon. There are so many comfortable spots to sit in! The pool was lovely and refreshing when it was hot mid afternoon and looked beautiful in the evening. Tuscany is stunning, there's so much to explore - would heavily recommend a car for that. In walking distance there are a couple of very delicious restaurants and if you're feeling adventurous you can walk to the monostary nearby which is definitely worth visiting. Thank you Guido!

Lovely home in villa with garden and pool
A beautiful stay in Tuscany perfect for relaxing on the property and visiting towns.
Condo rentals with a pool

Stylish Italian Apartment w/ Pool, Near Beach!
We had a wonderful time in the apartment Mirto. Everything was thought of, we were warmly welcomed, there was a huge fruit bowl and wine. The amenities were especially great for families. Even a laundry basket was there. The outdoor area was indescribably beautiful. So much space. So much nature. This tranquility. Heavenly. We slept wonderfully. Beds are very comfortable. There are plenty of cabinets. The furnishings of all rooms are incredibly tasteful. We felt incredibly comfortable. Thank you for the wonderful time ♥️ We recommend a trip to the magical mountain village of Pitigliano, about 1 hour away.

Girasole Apartment
Amazing place, staff provides great service whenever needed

Amazing Calamoresca
Bright and cozy house exactly as shown in the photographs and description. Functional kitchen and spacious and well-disposed spaces. Clean and modern bathrooms. Terrace with sea view and fantastic views at every hour of the day and night, we were mesmerized! Quiet and relaxing setting within the Cala Moresca consortium that we already knew but was able to amaze us again with the well-kept and very clean common spaces for the amazing pool set in the rocks with an attached descent to the crystal clear sea. Top! Finally, a delightful and very helpful owner who made us feel at home. Absolutely repeatable.

Il Granaio apartment Il Fienile with pool.
We stayed a week in one of the barn houses. The property is immersed in the Maremma countryside where the peace and sounds of nature reign. A few minutes away from vegetable shops, typical products and supermarkets. The nearby beaches are easily accessible in a few minutes by car and suitable for families. Hosts have recommended beaches, restaurants, and things to do near the property. The house is simply furnished but everything is perfectly functional and functional, the garden that each apartment has is delicious, fresh and full of flowers. For us it was an ideal solution to be able to explore the area and have the privacy and tranquility we were looking for for our holidays.

Relax between Siena and Valdorcia
I stayed at this place for 4 nights with my partner at the beginning of June 2025. It was so homely, very tidy and clean, with lots of amenities and the host was very welcoming. The views were incredible. We had a car which made visiting other places super convenient. We definitely recommend and would love to come back one day!

House in the small village with private pool
Quaint and cozy countryside cottage in a small welcoming village for an authentic experience. An opportunity to slow down and explore the beautiful landscape. Responsive host with a well stocked kitchen. Grocery store nearby. Walking trails everywhere and hot springs accessible with a car.

Podere Casanovola, Il Sole apartment
We stayed with Maria and Rodolfo for four nights and felt very, very comfortable. The beautiful house is off the road in idyllic countryside, surrounded by a park-like garden; a Shangri-La in the Maremma. The house is conveniently located for exploring the sights of the surrounding area. Maria and Rodolfo are the friendliest, most considerate and pleasant hosts you could imagine. Thank you for everything!!

Podere Cupiano "La Costa"
Francesco is an excellent host. Podere Cupiano is a fantastic estate. The views are to die for. Sopratutto, the pool is amazing. Montieri is a super cute and friendly town nearby with great restaurants. You should also visit the restaurant at VIN Hotel, a ten minute walk away.
Home rentals with a private pool

Il Cipresso by Interhome
The house was amazing, especially the area and the views. Sitting outside and using the pool in this beautiful surrounding were absolutely fantastic. It's a very wie and lovely place with a very nice pizza oven and barbecue outside. The owner are very nice and the communication was really good. We would really like to come back. Thank you for everything and also for the nice olive oil!

Pino di Sopra, by Interhome
Agrotourismo Pino di Sopra is a beautiful set of rooms in a peaceful part of Tuscany off the beaten track. The house is set up as two apartments and two double rooms, so perfect for two families sharing or a group of friends where you can all have your own space. The pool is large and suitable for kids and adults alike. I would highly recommend staying here. Our only negative was that the host told us we had to communicate off platform with the key holders (owners) which I was uncomfortable with. I had trouble getting in touch with the key holders and the hosts did not respond to my messages for assistance or offer any support with this. Once I made contact via SMS the owners were very helpful and responsive. It there was undue stress in the lead up to our trip.

Casale Vitello by Interhome
We are very happy with this stay and we had a lovely time with very good exchanges.

Casa Frati by Interhome
Overall the location and charm of the property were stunning. Spacious bedrooms and living areas (beware uneven flooring, to be expected in an old farmhouse, my elderly father struggled). NOTE: we have not been asked for a cash deposit with Airbnb before and were surprised when a man came about 3 hours after we arrived to collect €400 cash. He spoke no English and used his phone to call someone who could speak to me. The host had not said he would be coming, or who he was. I contacted Airbnb support who said I could pay through the resolution centre. As others mentioned, there were no oil, salt, pepper etc, although a few dishwasher tablets. The jacuzzi and sauna work with tokens for €8 each. Didn’t use so not sure how long you get. BUT, this is a stunning property with unbeatable views in the heart of Tuscany, tucked away on a hillside down a gravel track. Would definitely book again. Pool is pristine, towels spotless, beds comfortable.

Meridiana by Interhome
Quality accommodation in a beautiful environment!

Val d'Orcia by Interhome
Awesome property! Super responsive host!

Casa la Selvolina, by Interhome
Very Kind and lovely guys, quiet and relaxing area. I loved it

Villa al Sole by Interhome
The house corresponded to the description in every way. It was exactly like the pictures. The landlord was very nice. He was always available and took care of everything. Everything top 👍👍👍👍 5 stars ⭐️⭐️⭐️⭐️⭐️
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- Giglio Island
- Lake Trasimeno
- Lake Bolsena
- Giannutri
- Feniglia
- Gulf of Baratti
- Cala Violina
- Kite Beach Fiumara
- Marina di Grosseto beach
- Spiaggia di Capo Bianco
- Spiaggia Di Sansone
- Avignonesi Winery Fattoria Le Capezzine
- Spiaggia Marina di Cecina
- Cala Di Forno
- Santa Maria della Scala
- Spiaggia Di Barbarossa
- CavallinoMatto
- Spiaggia Zuccale
- Spiaggia di Seccione - Portoferraio (li)
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Tenuta Le Velette
- Pubblico Palace
- Spiaggia Di Sottobomba
- Spiaggia della Padulella
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